The development of methodology for the concise stereoselective synthesis of nitrogen-containing heterocycles is an active area of research, owing to the prevalence of such structural motifs in natural products and bioactive compounds. The pyridine motif (and saturated variants thereof) is in particular widely represented in compounds of biological importance, and consequently methods for its stereoselective preparation are well represented in the literature. It is the specific aim of this research proposal to outline a new method for the stereoselective preparation of such heterocycles employing a metal catalyzed olefinic C- H bond alkenylation/azaelectrocyclization sequence. This strategy allows for the concise stereoselective synthesis of pyridines, providing rapid access to this important class of compounds from readily available starting materials. Polysubstituted pyridines, chiral saturated pyridines, and uniquely fused bicyclic pyridine systems are all readily accessible using this new strategy. The application of this methodology to the total synthesis of the bioactive aza sugar (-)-swainsonine is also outlined. The development of new methods to concisely prepare therapeutic drugs in the laboratory continues to be an active area of research. This research aims to develop such new methods, and to apply them toward the preparation of drugs of potential therapeutic value.